 In 1998, he started commenting on Sunday evening Serie A matches, making turns with Massimo Marianella.In 2002, he became the main "voice" of SKY Sport and, together with former Inter Milan defender Giuseppe Bergomi, he is now one of the most notorious and appreciated sporting commentators in Italy.After the World Cup he wrote a book about his experiences during his career and the 2006 World cup, entitled "Andiamo a Berlino" ("We're going to Berlin"), a reference to Caressa's exclamation at the end of Italy's World Cup semi-final victory against hosts Germany, which ended in a 2–0 victory after extra time; just a few seconds after Italy's second goal, scored by Alessandro Del Piero, Caressa shouted the phrase, expressing his joy for Italy's qualification for the World Cup final that would be played in Berlin.